Pet-friendly holiday rentals in Leeward

4.87 out of 5 average rating, 15 reviews

An outdoor screened-in patio is shown, featuring a colorful striped rug beneath a small table and two comfortable chairs. A hammock is draped nearby, creating a relaxing space surrounded by greenery that enhances the ambiance.

Villa in Long Bay Hills

Steady Winds Hideaway - Turtle Villa 1 King Bed

Discover your private oasis in our delightful 1-bedroom villa nestled amidst lush greenery. This is a very safe and high end residential neighborhood with patrol cars nearby. Conveniently located just a short stroll away from Long Bay beach, where breathtaking sunrises and unforgettable beach memories await. Our welcome packet is available after booking. It's great for first time visitors to the island! Need more room? Adjacent villas are available to accommodate your larger groups as well.

Guest house in Caicos Islands

The cottage is framed by lush greenery, featuring a front porch with screened walls. Mature trees provide shade, while a stone border enhances the garden area. The subtle design blends into the natural surroundings, creating a serene entryway to the home.

4.95 out of 5 average rating, 57 reviews

Waterfront Cottage w/Kayaks + SUV JEEP BOAT Opt

"Sweet Escape Guest Cottage" sits on a beautiful 1 acre waterfront property with a dockside patio to relax & chill. Enjoy the sunset on the canal or sit under the stars at night. 75 feet of oceanfront with a floating ez dock and complimentary ocean kayaks, paddle boards, snorkel gear, beach chairs, umbrella and beach towels. A cooler, frisbee, football and more. Your own double hammock in your private garden area off your screened in porch with south beach chairs. Gated Entry - remote provided.

4.98 out of 5 average rating, 50 reviews

A modern building stands beside a pristine swimming pool surrounded by palm trees. The pool area features multiple lounge chairs arranged around the clear blue water, reflecting the bright blue sky. The clean lines and light color palette of the architecture enhance the serene environment.

Apartment in Grace Bay

The ONE at Grace Bay

Discover paradise in our 2-bed, 2-bath condo nestled in the heart of Grace Bay! With its prime location, you'll be just steps away from the world-renowned, stunning turquoise waters and white sand beaches. Our condo offers a fully equipped kitchen, private patio, shared pool, BBQ area, and gym. Ideal for relaxation and exploration, immerse yourself in island life, local shops, and dining. Your perfect getaway begins here. Book now for an unforgettable experience. Follow @theoneatgracebay!

4.89 out of 5 average rating, 28 reviews

A serene outdoor space showcases a private pool surrounded by lush greenery. Comfortable lounge chairs are positioned near the water, and a large umbrella offers shade. A covered seating area is visible in the background, enhancing the relaxing atmosphere.

Villa in Grace Bay

HopeWell Villa West - 5 Minutes to Grace Bay Beach

Located 5 minutes from GraceBay Beach, is Hopewell Villa East. This spacious 2 bedrooms 2 bath house is located just 2 streets from Grace Bay Beach and Coco Bistro Restaurant, in a quiet peaceful and safe residential neighborhood. If you are looking for a modern, clean, affordable, kids and family-friendly rental and minutes away from some of the most beautiful beaches in the world, look no further! **We have rental cars,suv and van available. Please let me know if you are interested.**

4.88 out of 5 average rating, 179 reviews

A thatched-roof gazebo is positioned near the water, surrounded by sandy ground and lush vegetation. Palm trees sway gently, and a calm body of water is visible in the background, reflecting the bright blue sky with fluffy clouds.

Loft in Long Bay Hills

Best deal on island! On the water w/pool!

♥♥ The studio is a secluded get-away place apart from the tourist areas. It overlooks the lake of Juba Sound National Park. The studio is only a 10-minute drive to the world-famous Grace Bay Beach and Longbay Beach (kiteboarding beach)! Restaurants and nightlife are also close by. The studio is in a secure, quiet location where you can relax and enjoy your vacation. This studio is ideal for singles, couples, and kiteboarders. You will need to rent a car for better convenience and freedom!

4.82 out of 5 average rating, 102 reviews

The outdoor area features a private saltwater pool surrounded by a sun deck with lounge chairs. Tropical plants are positioned nearby, and a shaded seating area is created by a white umbrella. The villa’s modern architecture complements the serene outdoor setting.

Villa in Providenciales

BeachHaus Villa with ocean view and private pool

Newly renovated Villa. Enjoy breathtaking panoramic ocean views from your private terrace, or from your second floor master suite balcony in our bright and modern villa. Fully-equipped open concept kitchen featuring a gas range, and dishwasher. Reliable wifi. Master with , ensuite with rainforest and hand-shower, wood barn doors, and private balcony with outshower. Pool and outdoor living. Ideal for families. Safe, quiet and central neighborhood, 3 minute walk to the beach!

4.81 out of 5 average rating, 130 reviews

A modern three-story building features spacious balconies with outdoor seating. Expansive glass windows reflect the sky, while an inviting lawn with well-maintained greenery surrounds the structure, creating a serene environment.

Apartment in Grace Bay

Gated Condo in Grace Bay/ Short Walk to Everything

This studio in Grace Bay offers comfort and convenience. It's a few minutes walk to the beach, grocery stores, restaurants, activities, and a medical center. The Caicos Key condo is new and includes a 55-inch smart TV with Fire Stick, fast Wi-Fi, a dishwasher, and a washer/dryer combo. For your security, the property has a smart lock and is gated. Guests can also use the swimming pool and BBQ area. We aim to make your stay comfortable and can provide anything you need on demand.

4.92 out of 5 average rating, 128 reviews

A modern villa is showcased, with its sleek design complemented by lush tropical landscaping. A private plunge pool is visible, surrounded by wooden decking and lounge chairs. A small outdoor dining area and a barbecue grill are also present, creating a relaxing outdoor living space.

Villa in Long Bay Hills

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY

Take it easy at this dreamy, unique and tranquil getaway. Villa Infini brings privacy and relaxation all in one. Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway. Bali like plunge pool that can create amazing insta-worthy moments. Located in Long Bay! A 5 minute walk to Long Bay Beach, a 5 minute drive to the nearest grocery store and a 5 minute drive to Grace Bay Beach. Everything is 5 minutes away!!

Flat in Cooper Jack Bay Settlement

A freshwater pool is set within a sunlit area, bordered by vibrant bougainvillea flowers. A shaded gazebo is visible in the background, furnished for relaxation. The surrounding landscape features greenery, enhancing the tranquil environment near the water.

4.93 out of 5 average rating, 138 reviews

Poco Villa

Situated in the Discovery Bay Canal "Poco Villa" is a separated complete studio with a view of the canal and access to a freshwater pool and sun decK with bar and barbeque. The accommodation is a one a/c unit with a full kitchen living room and tv. Its a peacefull place surrounded by water. There are two units for rent on this property the other "Coco Villa" both being double occupancy. We do suggest our guests have a vehicle rental to explore the island.

Guest house in Leeward Settlement

4.97 out of 5 average rating, 114 reviews

"The Nest Cozy Cottage"

“The Nest” Spacious and modern 1 bedroom cottage sits amongst a well-manicured garden with majestic swaying palms. Less than 150 steps away from the famous Grace Bay Beach. This cozy sanctuary is quiet and bears the true beauty of itself, it’s perfect for honeymooners or if you’re just seeking for some quiet and down time. Complete with high-speed internet, cable TV and all amenities one need for the perfect vacation, The Nest is where you want to be.

4.88 out of 5 average rating, 48 reviews

A single-story villa is featured, characterized by a sloped roof and wide front porch. Large windows allow for ample natural light. Surrounding vegetation includes palm trees, enhancing the tropical setting. The front porch is furnished with chairs and a table, inviting outdoor relaxation.

Villa in North Caicos

Baldwin Camp Rental- Villa #2

Baldwin Camp Rental is located on the Island of North Caicos, Turks & Caicos Islands. The villa consists of 2 bedroom, 1 bath. Each villa is equipped with: -32 inch flat screen TV With IP android box -Wi-Fi -Iron/Iron board -Free Washer and Dryer on premises -Blow Dryer -Grill -Patio -Coffee Maker -Microwave -Flat top Stove -Air-conditioned Bed-Rooms -Ocean view Bed-Rooms- (Main Bedroom) -Smoke Detector -Fire Extinguisher - First Aid Kit

4.69 out of 5 average rating, 64 reviews

Flat in Providenciales

Jade’s Hideaway in Paradise…walk to the beach

This is a rare find, if available. See more on IG Heavenly.Hideaway At 1100sqft, this oversized luxury suite in the exclusive ‘Yacht Club’ is located in the premier Turtle Cove Marina. This is the perfect treat for couples, solo adventurers, and business travelers, offering spectacular sunset and sunrise views over the infinity pools in the back and the ocean views in the front, from the unit’s second floor balconies.

Popular amenities for Leeward pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 26 reviews

An aerial view of the house surrounded by lush greenery. The traditional structure features a large white roof and a spacious deck that overlooks the landscape. The garden is filled with vibrant foliage, creating a serene environment.

Home in Caicos Islands

Richmond Hill House

A light-filled living area features a comfortable sectional sofa and a dining table. Large sliding glass doors lead to the outdoor space, while a ceiling fan adds to the airy environment. A view of the kitchen and bar area is visible in the background.

4.95 out of 5 average rating, 22 reviews

Welcome to Hope's Cottage!

A private swimming pool is set within a sun-drenched deck surrounded by lush palm trees. A comfortable wooden chair is positioned nearby, providing a perfect view of the inviting, clear water. The area is enclosed by a wooden fence, ensuring seclusion.

Home in Leeward Settlement

4.71 out of 5 average rating, 82 reviews

Private Pool, Steps To Sand, Great Reviews

Home in Providenciales

New place to stay

Oceanside Turtle Cove Home

A serene outdoor area is highlighted by a rectangular pool, surrounded by a spacious tiled patio. Sunlight casts intricate shadows from a wooden pergola onto the pool's clear water, enhancing the tranquil ambiance. Sparse landscaping adds a touch of nature to the surroundings.

Home in Blue Hills, Providenciales

4.62 out of 5 average rating, 61 reviews

Enjoy a peaceful and affordable stay in Paradise ☺

A bright living area features large windows offering views of the lush surroundings and distant water. Comfortable seating, including a green sofa and an armchair, is arranged around a central coffee table. Natural light floods the space, highlighting the open, airy design.

Home in Long Bay Hills

4.69 out of 5 average rating, 13 reviews

Metopium - 2/1 Secluded Getaway

A well-maintained outdoor area features a swimming pool surrounded by a spacious deck. Six loungers are positioned nearby, offering a place to relax. A covered seating area is visible in the background, complemented by tropical landscaping, enhancing the serene ambiance.

4.96 out of 5 average rating, 55 reviews

Hopewell Villa East/Pool & walk to Gracebay Beach

A wooden pathway leads to the beach, framed by lush greenery and trees on either side. The sky is clear with scattered clouds, and the calm ocean waves can be seen in the distance. This inviting walk offers a serene approach to the shore.

Home in Long Bay Hills

4.75 out of 5 average rating, 4 reviews

Maison Doree 2- Bedroom Cottage with Private Pool

Pet-friendly home rentals with a pool

A communal pool is framed by modern condominium buildings, with lounge chairs arranged on the pool deck. Lush greenery lines the perimeter, and tall palm trees sway gently in the background under a bright blue sky scattered with clouds.

4.86 out of 5 average rating, 22 reviews

Grace Bay View Top Floor Condo

A clear swimming pool is surrounded by palm trees, featuring a connected hot tub nestled at one end. Comfortable lounge chairs are positioned nearby, providing options for relaxation. Soft lighting adds ambiance around the pool area, enhancing the tranquil outdoor setting.

4.93 out of 5 average rating, 30 reviews

Perfect Getaway - 2 Bdrm Condo 2mins from Beach

Flat

New place to stay

Grace Bay Studio 05

A bright bedroom features large windows that provide expansive views of the turquoise ocean. A spacious bed with light linens is centered in the room, complemented by a white dresser and a cozy chair near the window. Natural light enhances the airy atmosphere.

Villa in Turtle Cove

4.81 out of 5 average rating, 70 reviews

Nirvana's Nest

4.94 out of 5 average rating, 18 reviews

A wooden chair is positioned on a dock overlooking clear turquoise waters. A towel is draped over the chair, and the sky above is bright and clear, punctuated by a few light clouds. The tranquil setting invites relaxation and enjoyment of the scenic views.

Villa in Providenciales

Turks & Caicos Oceanfront Villa w/Pool and Dock

An aerial view captures the layout of the private complex, featuring manicured gardens, a central pool area surrounded by greenery, and two multi-story buildings with terracotta roofs. The open space includes pathways, palm trees, and various tropical plants, providing a serene atmosphere.

Townhouse in Venetian Road Settlement

A Piece of Paradise

Flat in Providenciales

New place to stay

Spacious 1BR Retreat w/ Patio Pool peaceful

Cottage in Venetian Road Settlement

Lounge chairs are positioned beside a private pool, offering an unobstructed view of the turquoise ocean. A small table sits between the chairs, complementing the serene outdoor space surrounded by lush palms and vibrant greenery.

4.85 out of 5 average rating, 85 reviews

Sunrise Ridge Amazing 2 Bed Home

Private, pet-friendly home rentals

The outdoor area features a shared pool surrounded by lush greenery. Lounge chairs are positioned on the deck, offering a space for relaxation. Bright sunlight reflects off the turquoise water, while tall palm trees enhance the tropical setting.

4.64 out of 5 average rating, 56 reviews

Walk To Beach & Shops! Beautiful Patio/Pool-CV41

A private balcony features a pergola overhead, offering stunning ocean views. Two chairs are positioned beside a small table, enhancing the serene outdoor space. The coastal landscape stretches into the distance, complemented by a clear blue sky.

Home in Providenciales

4.71 out of 5 average rating, 24 reviews

Walk to Grace Bay, Pool, Views! (#2)

4.72 out of 5 average rating, 60 reviews

15% Off Oct- Walk to Grace Bay-Pool Views! Z-B103

4.76 out of 5 average rating, 34 reviews

15% Off October! Grace Bay Ocean Views! Z102

The outdoor area features a shared pool surrounded by tropical landscaping. Lounge chairs are positioned beneath a large umbrella. A wooden deck frames the pool, providing a relaxing space to enjoy the sun. Lush greenery and colorful flowers enhance the inviting atmosphere.

Home in Providenciales

4.8 out of 5 average rating, 60 reviews

Walk to Grace Bay, Pool, Views! (#4)

A spacious outdoor pool area is surrounded by palm trees and vibrant flowers, featuring a covered gazebo in the background. Lounge chairs are arranged along the poolside, while two woven chairs and a small table with a flower are positioned in the foreground.

Flat in Providenciales

4.77 out of 5 average rating, 109 reviews

Stunning Yacht Club, Short Walk to Beach W/Pool!

A tranquil pool area showcases a spacious swimming pool surrounded by lush greenery. Lounge chairs are positioned along the pool, inviting relaxation. The open space is filled with sunlight, emphasizing the vibrant colors of the tropical plants that provide a serene backdrop.

4.66 out of 5 average rating, 38 reviews

Walk To Beach & Shops! Beautiful Patio/Pool-CV41

A serene shared pool area is surrounded by lush tropical landscaping. Sun loungers are positioned around the pool, offering spaces for relaxation. The clear water in the pool reflects the bright blue sky, creating a tranquil outdoor setting.